American Airlines Boston to Chicago Flights

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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap American Airlines flights from Boston to Chicago. Compare airline ticket prices and book air tickets starting from $67 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of American Airlines, arrivals and departure details below.

Find Cheap Airfare Boston (MA) — Chicago (IL) by American Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in january: one-way - $67, two-way – $115.

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Cheap Flights from Boston to Chicago by American Airlines

Look at the list of plane tickets for the most popular direct and connecting flights by American Airlines, their prices start from $67. The fastest nonstop flight takes 3h 1m. The fastest connecting flight — 4h 45m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $67 Find flight	5:15 am Boston Logan	7:19 am Chicago O'Hare International	3h 4m	American Airlines	AA3452
from $67 Find flight	12:00 pm Boston Logan	2:01 pm Chicago O'Hare International	3h 1m	American Airlines	AA1239
from $67 Find flight	2:41 pm Boston Logan	4:43 pm Chicago O'Hare International	3h 2m	American Airlines	AA514
from $67 Find flight	1:29 pm Boston Logan	3:36 pm Chicago O'Hare International	3h 7m	American Airlines	AA4392
from $101 Find flight	5:15 pm Boston Logan	7:22 pm Chicago O'Hare International	3h 7m	American Airlines	AA4629
from $124 Find flight	10:30 am Boston Logan	12:31 pm Chicago O'Hare International	3h 1m	American Airlines	AA3569
from $96 Find flight	6:00 am Boston Logan	10:06 pm Chicago O'Hare International	17h 6m layover 13h 1m - New York	American Airlines	AA4505 NK3386
from $144 Find flight	1:00 pm Boston Logan	8:33 pm Chicago O'Hare International	8h 33m layover 4h 34m - New York	American Airlines	AA4342 AA1263
from $161 Find flight	5:30 pm Boston Logan	10:05 pm Chicago O'Hare International	5h 35m layover 1h 22m - Washington D.C.	American Airlines	AA4409 AA1630
from $161 Find flight	8:30 am Boston Logan	1:14 pm Chicago O'Hare International	5h 44m layover 1h 42m - Washington D.C.	American Airlines	AA2951 AA489
from $161 Find flight	8:00 am Boston Logan	11:45 am Chicago O'Hare International	4h 45m layover 0h 33m - New York	American Airlines	AA4349 AA2084
from $161 Find flight	4:13 pm Boston Logan	10:53 pm Chicago O'Hare International	7h 40m layover 3h 34m - Philadelphia	American Airlines	AA2922 AA2554
from $161 Find flight	7:00 am Boston Logan	11:00 am Chicago O'Hare International	5h 0m layover 0h 52m - Washington D.C.	American Airlines	AA2565 AA1200
from $161 Find flight	5:59 pm Boston Logan	10:53 pm Chicago O'Hare International	5h 54m layover 1h 49m - Philadelphia	American Airlines	AA1408 AA2554
from $164 Find flight	8:30 am Boston Logan	3:40 pm Chicago O'Hare International	8h 10m layover 3h 26m - Charlotte	American Airlines	AA2320 AA614
from $180 Find flight	12:35 pm Boston Logan	5:35 pm Chicago O'Hare International	6h 0m layover 1h 51m - New York	American Airlines	AA4402 AA532

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 12/22/2024

American Airlines Flight Schedule Boston to Chicago

Below is a detailed 2025 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.

Departure	Flight Details	Flight Time	Price
10:30 am — 12:31 pm	10:30 am — 12:31 pm AA3569 American Airlines Boston — Chicago	3h 1m	Find flight from$124
12:00 pm — 2:01 pm	12:00 pm — 2:01 pm AA1239 American Airlines Boston — Chicago	3h 1m	Find flight from$67
1:29 pm — 3:36 pm	1:29 pm — 3:36 pm AA4392 American Airlines Boston — Chicago	3h 7m	Find flight from$67
2:41 pm — 4:43 pm	2:41 pm — 4:43 pm AA514 American Airlines Boston — Chicago	3h 2m	Find flight from$67
5:15 am — 7:19 am	5:15 am — 7:19 am AA3452 American Airlines Boston — Chicago	3h 4m	Find flight from$67
5:15 pm — 7:22 pm	5:15 pm — 7:22 pm AA4629 American Airlines Boston — Chicago	3h 7m	Find flight from$101
10:35 am — 5:35 pm	10:35 am — 11:59 am AA4566 American Airlines Boston — New York 3h 51m stop 3:50 pm — 5:35 pm AA532 American Airlines New York — Chicago	8h including layover	Find flight from$164
11:03 am — 4:09 pm	11:03 am — 12:56 pm AA4350 American Airlines Boston — Washington D.C. 1h 53m stop 2:49 pm — 4:09 pm AA1682 American Airlines Washington D.C. — Chicago	6h 6m including layover	Find flight from$164
11:12 am — 5:31 pm	11:12 am — 12:46 pm AA1776 American Airlines Boston — Philadelphia 3h 14m stop 4:00 pm — 5:31 pm AA1090 American Airlines Philadelphia — Chicago	7h 19m including layover	Find flight from$164
12:19 pm — 7:11 pm	12:19 pm — 2:55 pm AA3252 American Airlines Boston — Charlotte 3h 6m stop 6:01 pm — 7:11 pm AA2488 American Airlines Charlotte — Chicago	7h 52m including layover	Find flight from$164
1:00 pm — 10:06 pm	1:00 pm — 2:16 pm AA4342 American Airlines Boston — New York 6h 13m stop 8:29 pm — 10:06 pm NK3386 Spirit Airlines New York — Chicago	10h 6m including layover	Find flight from$96
3:45 pm — 10:05 pm	3:45 pm — 5:31 pm AA1423 American Airlines Boston — Washington D.C. 3h 14m stop 8:45 pm — 10:05 pm AA1630 American Airlines Washington D.C. — Chicago	7h 20m including layover	Find flight from$164
4:13 pm — 10:53 pm	4:13 pm — 5:46 pm AA2922 American Airlines Boston — Philadelphia 3h 34m stop 9:20 pm — 10:53 pm AA2554 American Airlines Philadelphia — Chicago	7h 40m including layover	Find flight from$161
4:30 pm — 10:05 pm	4:30 pm — 6:20 pm AA4344 American Airlines Boston — Washington D.C. 2h 25m stop 8:45 pm — 10:05 pm AA1630 American Airlines Washington D.C. — Chicago	6h 35m including layover	Find flight from$164
6:00 am — 10:06 pm	6:00 am — 7:28 am AA4505 American Airlines Boston — New York 13h 1m stop 8:29 pm — 10:06 pm NK3386 Spirit Airlines New York — Chicago	17h 6m including layover	Find flight from$96
6:00 am — 1:58 pm	6:00 am — 7:28 am AA4505 American Airlines Boston — New York 4h 47m stop 12:15 pm — 1:58 pm AA3219 American Airlines New York — Chicago	8h 58m including layover	Find flight from$144
7:00 am — 11:00 am	7:00 am — 8:52 am AA2565 American Airlines Boston — Washington D.C. 52m stop 9:44 am — 11:00 am AA1200 American Airlines Washington D.C. — Chicago	5h including layover	Find flight from$161
7:00 am — 11:13 am	7:00 am — 8:42 am AA2764 American Airlines Boston — Philadelphia 1h stop 9:42 am — 11:13 am AA2095 American Airlines Philadelphia — Chicago	5h 13m including layover	Find flight from$164
8:00 am — 11:45 am	8:00 am — 9:27 am AA4349 American Airlines Boston — New York 33m stop 10:00 am — 11:45 am AA2084 American Airlines New York — Chicago	4h 45m including layover	Find flight from$161
8:30 am — 1:14 pm	8:30 am — 10:17 am AA2951 American Airlines Boston — Washington D.C. 1h 42m stop 11:59 am — 1:14 pm AA489 American Airlines Washington D.C. — Chicago	5h 44m including layover	Find flight from$161
9:30 am — 3:09 pm	9:30 am — 11:03 am AA1859 American Airlines Boston — Philadelphia 2h 38m stop 1:41 pm — 3:09 pm AA470 American Airlines Philadelphia — Chicago	6h 39m including layover	Find flight from$164
9:30 am — 2:10 pm	9:30 am — 12:02 pm AA1719 American Airlines Boston — Charlotte 58m stop 1:00 pm — 2:10 pm AA1052 American Airlines Charlotte — Chicago	5h 40m including layover	Find flight from$164

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 12/22/2024

Flight Information

There are 6 flights by American Airlines from Boston to Chicago every week with departures from Logan, Boston City Heliport, Boston RT128 Rail, Boston South Rail. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:00 am to 9:30 am. Nonstop flight is 3h 1m. The time difference between Boston and Chicago is 1h.

The fastest flight 3h 1m
Average flight time 3h 3m
The earliest flight 10:00 am
The latest flight 9:30 am
Distance 852 ml

The cheapest months for traveling to Chicago are november (from 67 $).

The cheapest flight by American Airlines that our users were able to find is $67. This airfare is economy class on one-way AA3452 flight for November 12, 2024 leaving Logan in Boston at 5:15 am, it includes all taxes and additional fees.

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American Airlines Airplanes on the Route

List of the most popular American Airlines airplanes flying from Boston to Chicago:

Boeing 737-800

from $67

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Embraer 175 (short wing)

from $67

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Embraer 170

from $124

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Airbus A319

from $161

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Airbus A321

from $161

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Airbus A320

from $164

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Other Popular Airlines on the Route

Besides American Airlines there are other 7 airline carriers between Boston and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Boston to Chicago.

Nonstop flights

There are 13 direct flights every day from Boston. Airlines and fares are below:

UA - United Airlines

from $122

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Connecting Flights

List of flights with layovers (1 and more stops):

PD - Porter Airlines

from $317

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UA - United Airlines

from $132

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NK - Spirit Airlines

from $62

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F9 - Frontier Airlines

from $67

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OS - Austrian Airlines

from $6303

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LX - SWISS International Air Lines

from $6019

Find
TS - Air Transat

from $338

Find

See more connecting flights

How to book an air ticket yourself?

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